Comparing Industrial Amination Reactions in a Combined Class and Laboratory Green Chemistry Assignment

This article describes a comparative assignment developed for a third-year undergraduate organic synthesis course involving a combined laboratory experiment and class exercise. In this assignment, students compare the sustainability of two industrial amination reactions to form the same target molecule (4-(n-hexylamino)­benzonitrile): a nucleophilic aromatic substitution procedure (SNAr) provided in the class exercise, and a Buchwald–Hartwig (B–H) amination procedure completed in the laboratory. The assignment is structured using a “case-study” format to provide appropriate context. Students use industrial solvent and reagent substitution guides, complete process mass intensity calculations, and apply the Twelve Principles of Green Chemistry to compare and contrast the SNAr and B–H reactions. They finally recommend a preferred reaction procedure after considering multiple sustainability concepts in their analyses. The assignment is highly adaptable as different industry guides may be used and the SNAr reaction procedure is easily modified. Ultimately, students learn to apply sustainable chemistry principles to industrially relevant reactions, an important skill for their future careers.